CN101747996B - Method of improving oil compositions - Google Patents

Method of improving oil compositions Download PDF

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Publication number
CN101747996B
CN101747996B CN2009102580091A CN200910258009A CN101747996B CN 101747996 B CN101747996 B CN 101747996B CN 2009102580091 A CN2009102580091 A CN 2009102580091A CN 200910258009 A CN200910258009 A CN 200910258009A CN 101747996 B CN101747996 B CN 101747996B
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oil
fatty acid
nitrogen
atoms
derived
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CN101747996A (en
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R·D·泰克
D·里亚诺-格尔多
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Infineum International Ltd
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Infineum International Ltd
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • C10L10/16—Pour-point depressants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/04—Well-defined hydrocarbons aliphatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
    • C10M149/22—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
    • C10L2200/0259—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Fats And Perfumes (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

A method of improving the low temperature properties of an oil comprising fatty acid alkyl esters derived from plant or animal materials, wherein at least 5% by weight of the fatty acid alkyl esters are derived from C 16 - C 22 saturated fatty acids. The method comprising reacting at least a portion of the oil with a polyalkylene polyamine or an imidazoline compound carrying both a poly-alkylene imine substituent and at least one primary amine group.

Description

Improve the method for oil compositions
The application relates to a kind of low-temperature performance to the oil that obtains from plant or animal material and carries out Innovative method.
The oil that is more and more obtained by plant or animal is used as fuel applications, particularly, and as the part or all of substitute of midbarrel fuel such as the diesel oil of petroleum derivation.In general, above-mentioned fuel is considered to " biofuel " or " biofuel ".Biofuel can be obtained by a lot of sources.Wherein modal is by the alkyl ester of plant such as the lipid acid that extracts in Semen Brassicae campestris, sunflower seeds etc., normally methyl ester.Such fuel is commonly called FAME (fatty acid methyl ester, fatty acid methyl ester).
Exist the motivating force on environment to use this class A fuel A with encouragement, because it is from renewable resources.The few sign of petroleum derivation fuel of the damage ratio a great deal of that when simultaneously, also existing burning, biofuel produces.
The oil fuel that is obtained by plant or animal material contains such component, normal chain alkanoic acid methyl esters for example, described component is easy to be precipitated as crystal large, sheet at low temperatures, and perhaps therefore the glomerate wax of shape also form the structure of gel, can cause like this fuel to lose flowability.The minimum temperature that fuel still can flow is pour point.
Along with the reduction of fuel temperature and reach pour point, come the difficulty of transport fuel to increase by pipeline and pump.In addition, during higher than pour point, the wax of crystal easily stops up burning line, filter screen and strainer in temperature.There has been sufficient understanding this area to these problems, has proposed multiple additives, wherein much by commercialization, reduces the pour point of oil fuel, comprises for from oil neutralization from plant or the oil fuel that obtains of animal material.Size and its shape of change of the crystal of other additives and commercial wax for reducing to form similarly, have also been proposed.Owing to being not easy blocking filter, so the less crystal of desired size.Specific additive can stop wax crystallization to become the tendency of platelet, replaces the form that forms needle-like.Compare with platelet, the pin that obtains relatively more easily passes through strainer; Perhaps generate the crystal layer of porous on strainer.These additives can also make crystal wax keep suspended state in fuel, have slowed down sedimentation and have therefore helped to stop and stopped up.
The cryogenic properties of the oil that is obtained by plant or animal material is by the content of saturated lipid acid in oil, the C that particularly exists to a great extent 16-C 22The ratio of saturated fatty acid determines.The most debatable is methyl esters and the ethyl ester of above-mentioned acid.Substance crystallization in fatty acid ester blends out temperature or under very difficult when above-mentioned oil is transported and operates.Containing the oil of seldom measuring polyunsaturated fatty acid ester sometimes can process by conventional additive and successfully improve its cryogenic properties.But, have been found that traditional additive to contain even low levels relatively particularly derived from the not effect of oil of palmitinic acid and stearic ester.
Although there are above-mentioned these problems, still need to utilize the C that contains by plant or animal material acquisition 16-C 22The oil of saturated fatty acid.This is because these oil are to be obtained by relatively cheap and rich in natural resources.The invention provides a kind of these oil and transport at low temperatures solution with operational issue.
According to the present invention, the method for a kind of improvement by the cryogenic properties of the oil that contains fatty acid alkyl ester of plant or animal material acquisition is provided, wherein the fatty acid alkyl ester of at least 5 % by weight is C 16-C 22The ester of saturated fatty acid, the method comprise that wherein at least one nitrogen-atoms exists with the form of primary amine with at least a portion oil and at least a compound reaction with 3 or more nitrogen-atoms; Wherein at least a compound with 3 or more nitrogen-atoms contains polyalkylene polyamine or imidazolinium compounds, and it is with polyalkyleneimine substituting group and at least one primary amine group.
In the context of the present invention, can comprise one or more in the improvement in pour point, cloud point, cold filter clogging temperature (CFPP) or the test of other operability about the improvement of the cryogenic properties of oil.Those skilled in the art know suitable test.The improvement of preferred cryogenic properties comprises to pour point and/or to the improvement of CFPP.
Do not wish to be subject to any one theory, should think various types of mixtures of the fatty acid ester of deteriorated low temperature performance that make are carried out amidation, " additive " of the cryogenic properties that can effectively improve the oil that contains a large amount of these esters is provided.Should " additive " be that directly derivative ester reaction in－situ makes with containing debatable saturated fatty acid for compound by will contain 3 or more nitrogen-atoms.As known in the art, for example the reaction of methyl esters and amine formation acid amides is easy to carry out.
Be preferably the % by weight in weight of oil 0.05-10 with the ratio of the oil of the compound reaction with 3 or more nitrogen-atoms, more be preferably the 0.05-2 % by weight, for example the 0.05-1 % by weight.
In case after oil and the compound reaction with 3 or more nitrogen-atoms, can independently use, for example, as pure biofuel, or mix use with petroleum derived oils with any ratio.
In a preferred implementation, used at least a extra lipid acid.The preferred mixture that uses lipid acid, for example, the mixture of the lipid acid that is obtained by plant or animal material.Described at least a lipid acid and oil and at least a compound with 3 or more nitrogen-atoms together react, and perhaps add in oil.Described at least a lipid acid and described at least a compound with 3 or more nitrogen-atoms can add in oil in any order.
By using at least a lipid acid, can further improve by plant or animal material obtain contain at least 5 % by weight derived from C 16-C 22The cryogenic properties of the oil of the fatty acid alkyl ester of polyunsaturated fatty acid ester.
What expect is to have in the compound of 3 or more nitrogen-atoms one (or a plurality of, if present) primary amine group and fatty acid alkyl ester react to form acid amides.As mentioned above, this reaction is favourable, and can promote by the heating of gentleness.On compound, other nitrogen-atoms can be, for example, and secondary amine or tertiary amine.More not preferred by the acid amides that above-mentioned amine groups generates, think that therefore it keeps not reacting under fatty acid alkyl ester exists.Think at present and add lipid acid can promote one or more other nitrogen-atoms to produce salt.
The below will describe various character of the present invention in detail.
The mixture of fatty acid alkyl ester
In the fatty acid alkyl ester mixture, at least 5 % by weight are derived from C 16-C 22Saturated fatty acid.Preferably at least 10%, more preferably at least 20%, more preferred at least 30% fatty acid alkyl ester mixture is derived from C 16-C 22Saturated fatty acid.Be preferably methyl esters or ethyl ester, particularly methyl esters.
In a preferred implementation, derived from C 16-C 22The fatty acid alkyl ester of saturated fatty acid comprises Uniphat A60, methyl stearate, perhaps its mixture.
Preferably derived from C 16-C 22The amount of the mixture of the fatty acid alkyl ester of saturated fatty acid is no more than 60 % by weight.In fatty acid ester blends, the major part of residuum preferably includes derived from those of unsaturated fatty acids.
The indefiniteness example of suitable material comprises plam oil methyl esters (PME), soybean oil methyl ester (SME) and rapeseed methylester (RME).The mixture that the material that is obtained by different sources is arranged that also is fit to, for example, the mixture of PME and rapeseed methylester (RME) or similar mixture.
Compound with 3 or more nitrogen-atoms
Have at least 3 nitrogen-atoms with the compound of oil reaction.At least one in these nitrogen-atoms exists with the form of primary amine.
In one embodiment, the compound that has 3 or more nitrogen-atoms is (i) polyalkylene polyamine.
Suitable for those comprise the material of the amine nitrogen that connects by alkylidene bridge, wherein amine nitrogen can be primary, the second month in a season and/or uncle, prerequisite is that at least one amine nitrogen is primary amine group.Polyamines can be straight chain, wherein all amine groups be uncle or Zhong Jituan, perhaps can contain ring-type or branching the part or both all contain, in this case, also have tertiary amine group, again, prerequisite is that at least one amine nitrogen is primary amine group.Alkylidene group can be identical or different within a molecule.Preferred ethylidene or propylidene, the most preferred ethylidene.
The indefiniteness example of suitable polyalkylene polyamine comprises diethylenetriamine (DETA), Triethylenetetramine (TETA) (TETA), tetren (TEPA), penten (PEHA) and similar homologue.Usually the polyalkylene polyamine that has 5 or more nitrogen-atoms is better than having 4 or the polyalkylene polyamine of a nitrogen-atoms still less.
The mixture of polyalkylene polyamine is also suitable.As known in the art, can be easy to obtain these materials, and these materials contain the polyalkylene polyamine of various size.It is commonly called PAM.It can define by the average nitrogen-atoms number that per molecule in component contains, and the preferred per molecule 5-8.5 of this average nitrogen-atoms number more has preferred 6.8-8, for example 6.8-7.5 nitrogen.Heavier material, so-called HPAM is also suitable, such as containing average 7 and 8 of per molecule, and the amine mixt of the polyamines of 9 optional nitrogen-atoms.
In another embodiment, the compound that has 3 or more nitrogen-atoms is: (ii) simultaneously with the imidazolinium compounds of polyalkyleneimine substituting group and at least one primary amine group.This compound can by for example with methyl esters and the polyalkylene polyamine of lipid acid or lipid acid (for example stearic acid or palmitinic acid), make such as TETA, TEPA, PEHA, PAM and analogue react.
Lipid acid
Preferred lipid acid is the unsaturated fatty acids with 16-20 carbon atom.C particularly preferably 18Unsaturated acid is such as oleic acid, linoleic acid plus linolenic acid.Described acid can be used as pure component and uses, but the preferred mixture that uses the lipid acid that is obtained by plant or animal material.The mixture of the lipid acid that is for example obtained by rapeseed oil, Yatall MA, Fructus Coriandri oil, soybean oil, Oleum Gossypii semen, sunflower oil, Viscotrol C, sweet oil, peanut oil, Semen Maydis oil, Prunus amygdalus oil, palm-kernel oil, Oleum Cocois, mustard seed oil, curcas oil, tallow and fish oil.More example comprises by corn, jute, sesame, Butyrospermum Parkii fruit, peanut and the derivative oil of linseed oil, and can be derived thus by method well known in the prior art.Has high C 18The oil of unsaturated fatty acids ratio is suitable, namely surpasses the C of 50 % by weight 18Unsaturated fatty acids preferably surpasses 70% or 85 % by weight.The lipid acid that is obtained by Yatall MA and rapeseed oil is specially suitable.
Can use in the present invention one or more common additives.Suitable common additive is that well known in the art those can effectively improve the additive of oil fuel cryogenic properties, and the additive that can improve other character of oil, such as slip additive, antioxidant, dispersion agent, washing agent and analogue.
In a preferred implementation, can use ethene polymers as being total to additive.The below will provide the example of ethylene copolymer.
Ethene polymers
Each polymkeric substance can be the multipolymer of homopolymer or ethene and other unsaturated monomers.
Preferred comonomer is unsaturated ester or ether monomer, simultaneously more preferred ester monomer.Preferred ethene unsaturated ester multipolymer also has the unit of following formula except having the unit by ethylene derivative:
-CR 3R 4-CHR 5-
R wherein 3Represent hydrogen or methyl, R 4Represent COOR 6, R wherein 6Representative has 1-12, the alkyl of preferred 1-9 carbon atom, and it is straight chain, if when perhaps having 3 or more carbon atom, it is branching, perhaps R 4Represent OOCR 7, R wherein 7Represent R 6Or H, and R 5Represent H or COOR 6
They can contain the multipolymer of ethene and vinyl unsaturated ester, perhaps its derivative.An example is the multipolymer of the ester of ethene and saturated alcohol and unsaturated carboxylic acid generation, but preferred ester is the ester that unsaturated alcohol and saturated acid form.The ethylene-vinyl ester copolymer is useful, the multipolymer of optimal ethylene-vinyl acetate, ethene-propionate, ethene-vinyl caproate, ethene-2 ethyl hexanoic acid vinyl acetate, ethene-sad vinyl acetate or ethene-vinyl versatate.Preferably, multipolymer contains the vinyl acetate of 5-40 % by weight, the vinyl acetate of more preferred 10-35 % by weight.Also can use the mixture of two kinds of multipolymers, for example in U.S. Patent No. 3,961, disclosed in 916.The Mn of multipolymer is preferably 1000-10000.If necessary, multipolymer can contain the unit derived from extra comonomer, for example terpolymer, tetrapolymer or higher multipolymer, and for example wherein extra comonomer is iso-butylene or diisobutylene or other unsaturated ester.
Other suitable comonomers comprise hydrocarbon monomer, such as propylene, just-and different-butylene, 1-hexene, 1-octene, Methyl-1-pentene vinyl cyclohexane and multiple alhpa olefin well known in the prior art, such as 1-decene, 1-laurylene, 1-tetradecylene, 1-n-Hexadecane and 1-octadecylene and composition thereof.
The present invention is described by the following examples.
Embodiment 1
To have C 16-C 22Saturates content is that the rapeseed methylester (RME) of 6.2 % by weight is the tetren reaction of 0.125 % by weight with amount.Reaction was carried out 4 hours in 140 ℃ under nitrogen protection.The pour point of untreated RME is-12 ℃.After completing with the reaction of TEPA, pour point eases down to-42 ℃.
Embodiment 2
With the stearic acid of the diethylenetriamine of 1-2 mole and 1 mole by refluxing 160 ℃ of reactions in dimethylbenzene.Reaction is removed excessive amine and solvent by vacuum distilling after finishing.1-amino-ethyl-2-heptadecyl-tetrahydroglyoxaline obtains as product.To have C 16-C 22Saturates content is that the soybean oil methyl ester (SME) of 14.6 % by weight is the tetrahydroglyoxaline reaction of 0.5 % by weight with amount.Reaction was carried out 4 hours in 150 ℃ under nitrogen protection.Add ethylene vinyl acetate (EVA) multipolymer of 0.6 % by weight in the SME, the pour point that records is-42 ℃.As a comparison, the pour point that comprises the unreacted SME of 0.6% EVA multipolymer is-6 ℃.
Embodiment 3
According to the ratio identical with embodiment 2 and reaction conditions, Triethylenetetramine (TETA) and stearic acid are reacted.1-(N-amino-ethyl-amino-ethyl)-2-heptadecyl-tetrahydroglyoxaline obtains as product.To contain C 16-C 22Saturates content is that the soybean oil methyl ester (SME) of 14.6 % by weight is the tetrahydroglyoxaline reaction of 0.5 % by weight with amount.Reaction was carried out 4 hours in 150 ℃ under nitrogen protection.Add ethylene vinyl acetate (EVA) multipolymer of 0.6 % by weight in the SME, the pour point that records is-51 ℃.As a comparison, the pour point that comprises the unreacted SME of 0.6% EVA multipolymer is-6 ℃.

Claims (21)

1. an improvement contains the method derived from the cryogenic properties of the oil of the fatty acid alkyl ester of plant or animal material, and wherein at least 5% fatty acid alkyl ester is derived from C 16-C 22Saturated fatty acid, the method comprise that at least one in described nitrogen-atoms exists with the form of primary amine group with the described oil of at least a portion and at least a compound reaction with 3 or more nitrogen-atoms; Wherein said at least a compound with 3 or more nitrogen-atoms contains polyalkylene polyamine or simultaneously with the imidazolinium compounds of polyalkyleneimine substituting group and at least one primary amine group.
2. the method for claim 1, wherein said polyalkylene polyamine has 5 or more nitrogen-atoms.
3. the method for claim 1, wherein said imidazolinium compounds are to make by methyl esters and polyalkylene polyamine reaction with lipid acid or lipid acid.
4. method as described in any one in claim 1-3 is wherein with the part oil of the compound reaction with 3 or the more nitrogen-atoms 0.05-10 % by weight for oil.
5. method as described in any one in claim 1-3 wherein saidly contains that this is comprised of methyl esters or ethyl ester derived from the oil base of the fatty acid alkyl ester of plant or animal material.
6. method as claimed in claim 4 wherein saidly contains that this is comprised of methyl esters or ethyl ester derived from the oil base of the fatty acid alkyl ester of plant or animal material.
7. method as described in any one in claim 1-3, wherein said derived from C 16-C 22At least 5 % by weight of the fatty acid alkyl ester of saturated fatty acid are by Uniphat A60, methyl stearate, and perhaps its mixture consists of.
8. method as claimed in claim 4, wherein said derived from C 16-C 22At least 5 % by weight of the fatty acid alkyl ester of saturated fatty acid are by Uniphat A60, methyl stearate, and perhaps its mixture consists of.
9. method as claimed in claim 5, wherein said derived from C 16-C 22At least 5 % by weight of the fatty acid alkyl ester of saturated fatty acid are by Uniphat A60, methyl stearate, and perhaps its mixture consists of.
10. method as described in any one in claim 1-3, wherein at least a lipid acid and oil and at least a compound one with 3 or more nitrogen-atoms react, and perhaps it are added in oil.
11. method as claimed in claim 4, wherein at least a lipid acid reacts with oil and at least a compound one with 3 or more nitrogen-atoms, perhaps it is added in oil.
12. method as claimed in claim 5, wherein at least a lipid acid reacts with oil and at least a compound one with 3 or more nitrogen-atoms, perhaps it is added in oil.
13. method as claimed in claim 7, wherein at least a lipid acid reacts with oil and at least a compound one with 3 or more nitrogen-atoms, perhaps it is added in oil.
14. method as claimed in claim 7, wherein said at least a lipid acid contains the mixture derived from the lipid acid of plant or animal material.
15. method as claimed in claim 14, wherein said mixture have the C that surpasses 50 % by weight 18Unsaturated fatty acids.
16. method as described in any one in claim 1-3, it further comprises in oil and adds ethene polymers.
17. method as claimed in claim 4, it further comprises in oil and adds ethene polymers.
18. method as claimed in claim 5, it further comprises in oil and adds ethene polymers.
19. method as claimed in claim 7, it further comprises in oil and adds ethene polymers.
20. method as claimed in claim 10, it further comprises in oil and adds ethene polymers.
21. method as described in claims 14 or 15, it further comprises in oil and adds ethene polymers.
CN2009102580091A 2008-12-09 2009-12-09 Method of improving oil compositions Expired - Fee Related CN101747996B (en)

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